Cellulose acetate fiber tobacco smoke filter and process of manufacturing the same

ABSTRACT

A tobacco smoke filter effective for removing harmful and irritating substances from the tobacco smoke comprises a rod-like cellulose acetate fiber mass and a lubricant applied to the fiber mass and comprising a polyalkylene glycol-fatty acid-succharose ester ether of the formula:   WHEREIN ONE OF R1 to R8 is a polyalkylene glycol ether residue, at least one other is an acyl group having two to 19 carbon atoms and all the remainder are a hydrogen atom, and a polyglycerolfatty acid ester in which the polyglycerol group has a degree of polymerization of two to three and the fatty acid has 12 to 22 carbon atoms, and, if desired, an edible mineral oil.

ed States ate Honda et a1.

[ 1 Sept. 4, 1973 CELLULOSE ACETATE FIBER TOBACCO SMOKE FILTER ANDPROCESS OF MANUFACTURING THE SAME [73] Assignee: Mitsubishi AcetateCompany Limited, Tokyo, Japan [22] Filed: Dec. 17, 1971 [21] Appl. No;209,434

[30] Foreign Application Priority Data Dec. 18, 1970 Japan 45/113215[52] US. Cl. 131/267, 131/269 [51} Int. Cl A241) 15/02 [58] Field ofSearch 131/261, 269

[56] References Cited UNITED STATES PATENTS 3,620,227 11/1971 Saito eta1 131/269 3,477,445 11/1969 Price et a1 131/267 3,443,566 5/1969 Yasudaet a1 131/267 OTHER PUBLICATIONS Organic Chemistry (Text) by Fieser andFieser Third Edition pub. by The Reinhold Publishing Corp. New

York 1956, pages 412,413 and 41.4 cited.

Primary ExaminerMelvin D. Rein Attorney-James E. Armstrong et a1.

[5 7] ABSTRACT A tobacco smoke filter effective for removing harmful andirritating substances from the tobacco smoke comprises a rod-likecellulose acetate fiber mass and a lubricant applied to the fiber massand comprising a polyalkylene glycol-fatty acid-succharose ester etherof the formula:

wherein one of R, to R is a polyalkylene glycol ether residue, at leastone other is an acyl group having two to 19 carbon atoms and all theremainder are a hydrogen atom, and a polyglycerol-fatty acid ester inwhich the polyglycerol group has a degree of polymerization of two tothree and the fatty acid has 12 to 22 carbon atoms, and, if desired, anedible mineral oil.

10 Claims, No Drawings CELLULOSE ACETATE FIBER TOBACCO SMOKE FILTER ANDPROCESS OF MANUFACTURING THE SAME The present invention relates to atobacco smoke filter and a process of manufacturing the same, moreparticularly, relates to a cellulose acetate fiber tobacco smoke filtercontaining a lubricant effective for removing substances harmful andirritating to health from the tobacco smoke and for enriching flavor andmildness of the tobacco smoke and a process of manufacturing the same.

In order to remove the harmful and irritating substances from thetobacco smoke, it is effective to filter the tobacco smoke through afilter composed of cellulose acetate fibers, filter paper, activatedcarbon, silica gel, polyethylene glycol or a composition of two or moreof the above materials. Especially, it is wellknown that the celluloseacetate fiber is a very effective material for removing nicotine, tarand other substances harmful and irritating to health. Accordingly, thecellulose acetate fiber is generally utilized for man ufacturing atobacco smoke filter.

In the manufacture of the tobacco smoke filter, it is necessary that thefilter fibers have the following properties;

(1) high processability in the formation of filter tip from filamenttow,

(2) high stability of filter form,

(3) high property of removed of harmful and irritating substance fromthe tobacco smoke, and

(4) a property of highly enriching the flavor and mildness of thetobacco smoke.

The tobacco smoke filter made of the filter fibers is required to have apertinent smoke permeability and a high filtering efficiency to harmfuland irritating substances such as tar, nicotine and other alkaloids.

Generally, the cellulose acetate filament tow usable for producing thetobacco smoke filter tips is prepared in a process wherein celluloseacetate flakes are dis solved into an organic solvent such as acetone,methylene chloride, and methanol, the solution is subjected todry-spinning process, and then spun filaments are associated into afilament tow.

The filament tow thus produced is subjected to subsequent processingsteps. In order to enhance the processability of the filament tow, thefilament tow is generally impregnated with an aqueous emulsioncontaining a lubricant mainly consisting of mineral oil emulsified'by aneutral surface active agent.

Therefore, the lubricant is required to impart to the filament tow ahigh processability and stability in continuous drawing, winding andother steps, a high uniformity of crimp on the filament tow without skipwhich means non-crimped portions of about 3/16 inch to about [2/16 inchin length in the crimped filament, and a high opening property when thefilament tow is opened'to a filament web. Further, it is desired thatthe lubricant enhance the effect of the filter tip on removal ofnicotine, tar or other harmful and irritating substances, and increasethe rigidity of the filter tip without increasing the resistance tosmoke flow through the filter tip. Still further, it is preferable thatthe lubricant impart to the cigarette smoke an enriched flavor andmildness.

It is known that fatty acid saccharose ester is applied as a lubricantto the filament tow for tobacco smoke filter. However, it is difficultto apply the fatty acid saccharose ester lubricant to the filament towuniformly due to low stability of the aqueous emulsion containing it.

That is, the low stability of the lubricant aqueous emulsion results inseparation of the lubricant from the aqueous emulsion, so that theconcentration of the lubricant in the aqueous emulsion changes with timeand the separated lubricant deposits on the periphery of the rollerdisposed in the lubricant bath and carrying the aqueous emulsion to thefilament tow.

Such non-uniform lubrication of the filament tow re sults in a number ofdisadvantages such as uneven crimps on the filament tow, high frictionalresistance of the filaments to each other and to the processing devicefor example, the filament tow guide members, rollers and others,frequent breakages of the filament, and formation of numerous fibrils onthe filament tows.

These disadvantages result in further uneven entanglements of thefilaments in the tow and still further result in an unevenfilament webwhen the filament tow is opened.

When the tobacco smoke filter tip is made from an unevenly lubricatedfilament tow as above, there results frequent generation ofelectro-static charges on the filaments. The electro-static chargecauses difficulty in rolling up of the filament web into a rod so thatthe rolling up operation is frequently stopped and the rolling upmachine must be subjected to frequent regulation and cleaning thereof.Further, the tobacco smoke filters from the unevenly lubricated filamenttow result in non-uniformity of the flavor and mildness of the tobaccosmoke.

The inventors have searched for a long time for a neutral surface activeagent effective for uniformly emulsifying the fatty acid saccharoseester and, if necessary, mineral oil into water without obstructing thebeneficial properties of the fatty acid saccharose ester such as theability to remove harmful and irritating substances from the tobaccosmoke and the property of enriching the flavor and mildness of tobaccosmoke.

From the study, it has been found that polyglycerine fatty acid ester isa neutral surface active agent suitable for use as the lubricant for thecellulose acetate filament tow.

One of objects of the present invention is to provide a celluloseacetate fiber tobacco smoke filter effective for removing harmful andirritating substances from tobacco smoke and a process of manufacturingthe same.

Another object of the present invention is to provide a celluloseacetate fiber tobacco smoke filter effective for imparting enrichedflavor and mildness to tobacco smoke and a process of manufacturing thesame.

A further object of the present invention is to provide a celluloseacetate fiber tobacco smoke filter having a pertinent rigidity andresistivity against smoke flow and a process of manufacturing the same.

The tobacco smoke filter of the present invention comprises ashort-length, rod-like cellulose acetate fiber mass and a lubricantapplied to the cellulose acetate fiber mass and containing five to 35parts by weight of a polyalkylene glycol-fatty acid saccharose esterether of the formula:

wherein one of R,, R R R R R R and R represents a monovalentpolyalkylene glycol ether residue, at least one other represents amonovalent acyl group having two to 19 carbon atoms and all theremainder represent a hydrogen atom, and five to 65 parts by weight ofan ester of a fatty acid having 12 to 22 carbon atoms with apolyglycerin having a degree of polymerization of two to three.

The cellulose acetate fiber tobacco smoke filter of the presentinvention is manufactured by impregnating a cellulose acetate filamenttow with an aqueous emulsion of a lubricant as mentioned above, crimpingthe filament tow, forming the crimped filament tow into tobacco smokefilter rod and cutting the rod into tips.

The fatty acid saccharose ester usable for the present invention is anester ether of disaccharide having one polyalkylene glycol ether residueand one or more fatty acid ester residue, that is, a member of an acylgroup, more concretely, in an ester ether of pyranose and furanose typedisaccharide represented by the formula:

wherein one of R R R R R R R R is a monovalent polyalkylene glycol etherresidue, at least one other of them is a monovalent fatty acid esterresidue having two to 19 carbon atoms and all the remainder are ahydrogen atom.

In the saccharide ester ether, the fatty acid ester residue, namely, theacyl group may be selected from the group consisting of acid residues oflauric acid, coconut fatty acid, palmitic acid, stearic acid, oleicacid, or beef tallow fatty acid, and the polyalkylene glycol etherreside may be an ether residue of polyethylene glycol, polypropyleneglycol, polyethylene-propylene glycol, polybutylene glycol and otherpolyalkylene glycol in which five to 30 mols of glycol units arepolymerized.

The polyglycerine fatty acid ester usable for the present invention isprepared by the ester reaction of a fatty acid, for example, lauricacid, coconut fatty acid, palmitic acid, stearic acid, oleic acid andbeef tallow fatty acid with a polyglycerine having a degree ofpolymerization of two to three which is obtained by heatpolycondensationof glycerine at a high temperature. The lubricant usable for the presentinvention contains five to 35 parts by weight of the polyalkylene glycolfatty acid saccharose ester ether and five to 65 parts by weight ofpolyglycerine fatty acid ester, and if desired, a mineral oil usable asa food additive or medical additive. It is necessary that the ediblemineral oil meets the Japanese Pharmacopoeia Standard Requirements as tophase, pH, contents of solid paraffins and sulfur compounds,nitronaphthalene test and sulfur color test and meets the U. S. FoodAdditive Standard Requirements as to the ultraviolet rays absorptiontest.

The lubricant usable for the present invention may contain certainneutral surface active agents other than the polyglycerine fatty acidester and usable as a food additive and medical additive.

The lubricant is emulsified into water preferably in a concentration of0.5 to l0 percent by weight and applied to the cellulose acetatefilament tow so as to leave 0.5 to 5.0 percent of the lubricant based onthe weight of the filament tow, on the filament tow.

The cellulose acetate filament tow thus lubricated is valuable forproducing a tobacco smoke filter in a favourable condition and forobtaining tobacco smoke filter tips having high benefits in chemical andphysical properties, that is, the removal of harmful and irritatingsubstances from tobacco smoke and the enrichment of flavour and mildnessof tobacco smoke.

In the manufacture of the tobacco smoke filter of the present invention,a cellulose acetate filament tow is impregnated with an aqueous emulsioncontaining a lubricant as stated hereinbefore so as to apply a desiredamount of the lubricant to the filament tow, the impregnated filamenttow is crimped at a desired crimp number by a crimper and then thecrimped filament tow is formed into filter rod. In the formation of thefilter rod, the crimped filament tow is conditioned to a desiredmoisture content, and opened into a filament web and rolled up withpaper into a rod form using a filter plug making machine. The rod is cutinto filter plugs and thereafter, further cut into filter tips ofdesired length.

The following specific examples will more particularly illustrate thepresent invention.

Example 1 A lubricant aqueous emulsion was prepared by emulsifying 3percent by weight of a lubricant consisting of 25 parts by weight ofpolyoxyethylene palmitic acid saccharose ester ether wherein thepolyoxyethylene group consisted of 20 mols of ethylene oxide, 15 partsby weight of polyglycerol laurate wherein the polyglycerol group had adegree of polymerization of three and 60 parts by weight of an ediblemineral oil satisfying the Japanese Pharmacopoeia Standard and the U. S.Food Additive Standard and had an SSU viscosity of at a temperature of37.8 C, into 97 percent by weight of water. The aqueous emulsion wascharged into a lubrication bath having a rotatable roller lower halfpart of which was immersed in the aqueous emul- SlOl'l.

A cellulose acetate filament tow having a Y-shaped cross-sectionalprofile, a single filament denier of four and a total denier of 43,000was impregnated with the aqueous emulsion by bringing the filament towinto contact with the rotatable roller periphery carrying the aqueousemulsion while continuously advancing it forwardly. By the aboveprocess, the lubricant was applied to the filament tow in a content ofapproximately of 0.8 percent based on the weight of the filament tow.

The filament tow thus impregnated was crimped by a crimper at a crimpnumber of approximately 18 crimps/25 mm, and the crimped filament towwas conditioned into a predetermined moisture content and thereafter,packed in a package box.

The filament tow was continuously drawn out from the package box anduniformly opened. Using a filter plug making machine, the open filamentweb was rolled up with paper to form a rod of 7.9 mm diameter and thenthe rod was cut into filter plugs of 102 mm length. The removalefficiency for alkaloid was determined- A filter plug was further cut toform it into filter tips of according to ultraviolet rays absorptionspectrum anal- 17 mm length. ysis.

For comparison, three kinds of Comparison Exam- The organoleptic testwas carried out by 20 panel l A, B and C were prepared by the sameprocedure 5 members with respect to the six items of flavor, taste, asabove except that the lubr ca contained 110 P smell, mildness, generalquality and others, and signifig y laul'ate (Comparison Example P Y Y'cant differences between the cigarettes for every item ethylene palmiticacid saccharose ester ether (Comparwere d d lson Example and P y ylaul'ate and P Referring to Table I, it is clear that the lubricant ofoxyethylene Palmitlc acid sacchal'ose ester ether Example 1 gives ahigher stability to the aqueous emul- (Comparison Example sion, a moreuniform appearance and a higher opening The filter tips from the presentexample and Comparproperty to the filament tow, a higher rigidity andison Examples A, B and C were attached to cigarette moval efficienciesfor tar and alkaloids to the filter tip ends by adhesive paper so as toobtain samples for orand richer mildness to the cigarette than those ofComganqlevtic test parison Examples A, B and C.

With respect to the present example and Comparison Examples A, B and C,the lubricant aqueous emulsions, E l 2 the impregnated filament tows,the filter tips and the cigarette with a filter tip were subjected tomeasure- The procedure of Example 1 was repeated us ng an ment in theitems as shown in Table l. aqueous emulsion containing five percent byweight of Table 1 shows the results of the measurements. a lubricantconsisting of 20 parts by weight of polyoxy- TABLE 1 Comparison exampleMaterial Item Example 1 A B C Emulsion Stability l. Excellent GoodGoodl. Unstable.

Crimping property Good do do G d,

Appearance of crimped Substantially no skip. Small number of skips.Substantially no skip. Small number of skips. l'ilammit Tow tom Openingproperty. Weight (g.) .s Rigidity (1/10 mm. Resistivity against ve tl t.1-1 0 ae nioigii $212110; a 39.2 39.0 38.5 33.2.

tar (percent). Removal eificiency for 33.8 n 29.4 32.1 30.7.

alkaloids (percent). I Cigarette Organolcptic test R1011 mildness Goodomewhat poor n1Ild- Poor mildness and a mess. slight oil-like smell.

Measuring methods for the items shown in Table l ethylene palmitic acidsacharose ester ether in which were as follows. the polyxoyethylenegroup consisted of 20 moles of The stability of the lubricant aqueousemulsion was ethylene oxide, 15 parts by weight of polyglycerollaudetermined by standing 3, 5 and 10 percent lubricant 40 rate in whichthe polyglycerol group had a degree of aqueous emulsions at atemperatures of 20, and polymenzimon of i by we'ght of y' 40 C for 10days and observing changes during the ethylene P- m wh'ch the Y Ystanding, and observed significant differences between group consistedof 15 P oxlfie and 55 the emulsions were recorded parts by weight of anedible mineral 01] which had an The crimping property of the filamenttow and the SSU gz 9 C and sausfymg the P appearance of the crimpedfilament tow were deter- 32 g Standard and the Food mined according tothe method of JIS L-l036, and sig- 1 we nificant differences between thefilament tows were re- After the step cellulose acetatfi corded amenttow containing 1.0 percent of the lubricant based on the weight of thefilament tow, was crimped at a crimp number of approximately 18crimps/2S mm by a crimper. The crimped filament tow was conditioned intoa predetermined moisture content and The opening property of thefilament tow was determined using a Sleddit Roll type opening device,and significant differences between the filament tows were recorded. k d

The weight of the filter tips of 17 mm length was P36 6 mm a packagemeasured, Filter tips similar to those of Example 1 were pre- Th i i iwas expressed by the depth (in 0 mm) pared from the filament tow thuspacked in the packof a recess formed on the periphery of the filter tipof age 17 mm length by pressing against it with a circle plate Forcomparison, a filter Up (Comparison Example D) of 12 mm diameter under aload of 300 was prepared by the same procedure as above using as Theresistivity against ventilation was expressed by lubr'cam the mlxture of'f Item of the pressure drop in mm "20 when the air was flowed JapanesePat. No. 319,066, consisting of parts by through the filter tip of 17 mmlength at a flow rate of weight of mirferal and 25 P by weight of am]/Sec ture of sorbitan .rnonolaurate with poly-oxyethylene sorbitanmonolaurate in which the polyoxyethylene group consisted of 20 mole ofethylene oxide in equiva' lent mol number.

The filter tips of Example 2 and Comparison Example D were attached tocigarette ends by adhesive The removal efficiency for tar was determinedby 65 having a cigarette with a filter tip of 17 mm length smoked by anautomatic smoking device and measuring the weights of the filter tipbefore and after smokmg. l

paper in order to prepare testing specimens for an organoleptic test.

With respect to Example 2 and Comparison Example D, the lubricantaqueous emulsions, impregnated filater tips of 12 mm length.

For comparison, the same procedure as above was repeated using alubricant consisting only of the mineral oil same as above (ComparisonExample E).

ment tows, filter tips and cigarettes with a filter tip were Th fil i fE l 3 d Comparison Exam- Subjec ed 1 measurement in the items 88 Show Inple E were attached to cigarette ends by adhesive paper Table 2. inorder to prepare testing specimens for organoleptic Table 2 shows allthe results of the measurements. test TABLE":

Material Item Example 2 Comparison Example D Emulsion StabilityExcellent Good.

Crimping property. Goo Do. Filament tow Appearance of crimped tow.Substantially no skip... Substantially no skip.

Opening property Excellent Good. Weight (g.) 0.11 0.11, Rigidity(l/lOrnm.) 8. 8.5. Resistivityagainstventilation (mm. 29.7.... 29.2.Filter ti 2 I Removal efficiency for tar (percent). 26 24. Removalelliclcncy for alkaloids 22 21.

(pert-cut). Cigarette ()rgunoluntlc test Rich taste and good Good.

mildness.

Referring to Table 2, it is evident that the lubricant of Example 2 issuperior in the stability of the aqueous emulsion, opening property ofthe filament tow, rigidity, resistivity against ventilating and removingefficiencies for tar and alkaloids of the filter tip and taste andmildness of the cigarette more than those of Comparison Example D.

Table 3 shows properties of the filter tips and the cigarettes ofExample 3 and Comparison Example E. From the table, it is clear that thefilter tips and the cigarettes of Example 3 are superior in rigidity,resistivity against ventilation, removal efficiencies for tar andalkaloids and organoleptic properties to those of Comparison Example E.

1 Rich taste and good mildness. I 2 Pool mildness and a slight oil-likesmell.

Example 3 A cellulose acetate filament tow having regular crosssection,a single filament denier of 4 and a total denier of 55,000 was subjectedto the same procedure as that of Example 1 using a 3 percent aqueousemulsion of a lubricant consisting of parts by weight of polyoxyethylenelauric acid saccharose ester ether wherein the polyoxyethylene groupconsisted of i2 mols of ethylene oxide, 20 parts by weight ofpolyglycerol laurate 'wherein said polyglycerol group had a degree ofpolymerization of two and 60 parts by weight of an edible mineral oilhaving an SSU viscosity of 120 at a temperature of 37.8 C and satisfyingthe Japanese Pharmacopoeia Standard and the U. S. Food AdditiveStandard. The cellulose acetate filament tow contained 1.0 percent ofthe lubricant based on the weight of the filament tow, crimped at acrimp number of approximately 18 crimps/ mm by a crimper, conditionedinto a predetermined moisture content and then packed into a packagebox.

Thereafter, the filament tow was continuously drawn out from the packagebox and uniformly opened. Using a filter plug making machine, the openfilament web was rolled up with paper to form a rod of 8.2 mm diameter,and the rod was cut into filter plugs of 72 mm length. The filter plugwas further out to form it into fil- Example 4 The same procedure asthat of Example 1 was repeated using a 5 percent aqueous emulsion of alubricant consisting of 20 parts by weight of polyoxyethylene lauricacid saccharose ester ether in which the polyoxyethylene group consistedof 12 mols of ethylene oxide, 20 parts by weight of polyglycerol lauratein which the polyglycerol group had a degree of polymerization of two,15 parts by weight of polyglycerol oleate in which the polyglycerolgroup had a degreeof polymerization of two, and 45 parts by weight of anedible mineral oil having an SSU viscosity of at 37.8 C and satisfyingthe Japanese Pharmacopoeia Standard and the U. S. Food AdditiveStandard. The cellulose acetate filament tow contained 1.0 percent ofthe lubricant based on the weight of the filament tow.

The properties of the resultant filter tip and the cigarette areillustrated in Table 4 shown below.

Example 5 The same procedure as that of Example 1 was repeated using a 5percent aqueous emulsion of a lubricant consisting of 35 parts by weightof polyoxyethylene oleic acid saccharose ester ether in which thepolyoxyethylene group consisted of 25 mols of ethylene oxide, 10 partsof polyglycerol oleate in which the polyglycerol group had a degree ofpolymerization of two and 55 parts by weight of an edible mineral oilsatisfying the Japanese Pharmacopoeia Standard and the U. S. FoodAdditive Standard and having an SSU viscosity of 100 at 37.8 C. Thecellulose acetate filament tow contained 1.3 percent of the lubricantbased on the weight of the filament tow.

For comparison, the same procedure as above was repeated except that thelubricant consisted only of the mineral oil (Comparison Example F).

The resultant filter tips and the cigarettes of Example and ComparisonExample F had the properties as shown in Table 4 below.

Example 6 which the polyglycerol group had a degree of polymerization oftwo, parts by weight of polyoxyethylene isostearate in which thepolyoxye'thylene consisted of 15 mols of ethylene oxide and 70 partsbyrweight of an edible mineral oil satisfying the Japanese PharmacopoeiaStandard and the U. S. Food Additive Standard and having an SSUviscosity of l at 37.8 C. The cellulose acetate filament tow contained1.7 percent of the lubricant based on the weight of the filament tow.

The resultant filter tip and cigarette had the properties as shown inTable 4 below.

7 Example 9 15 The same procedure as that of Example 1 was re- The SameProcgdure as that of Example was peated using a 10 percent aqueousemulsion of a t d using a 5 percent aqueo eml1l$l0fl of a lubricantconsisting of 20 parts by weight of polyprolubriCa consisting of 20Parts y welght'of PQ Y Y' pylene glycol lauric acid saccharose esterether in ethylene oleic acid saccharose ester ether in which the hi h hpolypropylene glycol group had a molecular polyoxyethylene groupconsisted of mols of ethylene 20 weight of approximately 400, 20 partsby weight of oxide, 60 parts of polyglycerol laurate wherein t epolyglycerol laurate in which the polyglycerol group polyglycerol grouphad a degree of: polymerl p of had a degree of polymerization of two and60 parts by twg d 20 parts by weight of an edible m e 011 weight of anedible mineral oil satisfying the Japanese isfying the JapanesePharmocopoeia Standard and h Pharmacopoeia Standard and the u. 5. FoodAdditive 3, Food Additive Standard and having an SSU vls- 25 Standardand having an SSU viscosity of 120 at 37.8 cosity of l00 at 37.8 C. Thecellulose acetate filament C. The cellulose acetate filament towcontained 1.0 tow contained 1.0 percent of the lubricant based on thepercent of the lubricant based on the weight of the filaweight of thefilament tow. ment tow.

The properties of the resultant filter tip and the ciga- The resultantfilter tip and the cigarette had the proprette are shown in Table 4below. erties as shown in Table 4 below.

" T TABLE d Example Comparison Example xample Material Item 4 5 F 6 7 80 {Weight 0.12 0.11 0.11 0.11 0.13 0.11 0.11 Rigidity (1/10 mm.) 8.4 8.58.6 8.5 8.3 8.3 8.4 Resistivity against ventilation 20.0 30.0 29.3 30.830.2 29.0 20.0 Filter tip (mm. H2O).

Removal elliciency for tor (percent)- 25 26 24 26 27 26 25 Removalcllicienoy for alkaloids 22 22 21 22 23 22 21 (percent). CigaretteOrganoleptic test (i) (a) (1) Good l Rich mildness. I A little Oil-likesmoll.

Rich taste and good mildncss.

Example 7 The same procedure as that of Example 1 was repeated using a2.5 percent aqueous emulsion of a lubricant consisting of 30 parts byweight of polyoxyethylene palmitic acid saccharose ester ether in whichthe polyoxyethylene group consisted of 20 mols of ethylene oxide, 60parts by weight of polyglycerol laurate in which the polyglycerol grouphad a degree of poly-' GHzO 1 IIZCORIS merization of two and 10 parts byweight of polyoxy- 11 0 01120115 ethylene isostearate in which thepolyoxyethylene RQCFCQ g group consisted of 15 mols of ethyleneoxide.The cellufi fi lose acetate filament tow contained 3.0 percent of the A)J) I lubricant based on the weight of the fiber tow. The resultantfilter tip and cigarette had the properties as shown in Table 4 below.wherein one of Rh R2. R3, R R5 R8. R7 and R" Example 8 represents apolyalkylene glycol ether residue, at least The same procedure as thatof Example 1 was reone other of them represents an acyl group having twopeated using a 10 percent aqueous emulsion of a to 19 carbon atoms andall the remainder represent a lubricant consisting of five parts byweight of polyoxyhydrogen atom, and five to 65 parts by weight of apolyethylene lauric acid saccharose ester ether in which thepolyoxyethylene group consisted of 20 mols of ethylene oxide, 10 partsby weight of polyglycerol laurate in glycerine fatty acid ester in whichthe polyglycerine residue has a degree of polymerization of two to threeand the fatty acid residue has 12 to 22 carbon atoms.

2. A tobacco smoke filter as claimed in claim 1, wherein said lubricantfurther comprises to 70 parts by weight of an edible mineral oil.

3. A tobacco smoke filter as claimed in claim 1, wherein the amount ofsaid lubricant in said fiber bundle is 0.5 to 5.0 percent based on theweight of said fiber bundle.

4. A tobacco smoke filter as claimed in claim 2, wherein the amount ofsaid lubricant in said fiber bundle is 0.5 to 5.0 percent based on theweight of said fiber bundle.

5. A tobacco smoke filter as claimed in claim 1, wherein saidpolyalkylene glycol ether residue is selected from the group consistingof the ether residues of polyethylene glycol, polypropylene glycol,polyethylene-propylene glycol and poly-butylene glycol.

6. A tobacco smoke filter as claimed in claim 1, wherein saidpolyalkylene glycol ether residue consists of five to 30 moles of glycolunits.

7. A tobacco smoke filter as claimed in claim 1, wherein said acyl groupis selected from the group consisting of acid residues of lauric acid,palmitic acid stearic acid, oleic acid, coconut fatty acid and beeftallow fatty acid.

8. A tobacco smoke filter as claimed in claim 1, wherein the fatty acidresidue of said polyglycerine fatty acid ester is selected from thegroup consisting of acid residues of lauric acid, palmitic acid, stearicacid,

oleic acid, coconut fatty acid and beef tallow fatty acid.

9. A process of manufacturing a cellulose acetate fiber tobacco smokefilter which comprises impregnating a cellulose acetate filament towwith an aqueous emulsion of a lubricant containing 5 to 35 parts byweight of a polyalkylene glycol fatty acid saccharose ether ester havingthe formula:

wherein one of R R R R R R R and R represents a polyalkylene glycolether residue, at least one other of them represents an acyl grouphaving two to 19 carbon atoms and all the remainder represent a hydrogenatom, and five to 65 parts by weight of a polyglycerine fatty acid esterin which the polyglycerine residue has a degree of polymerization of twoto three and the fatty acid residue has 12 to 22 carbon atoms, crimpingsaid impregnated filament tow and forming said crimped filament tow intotobacco smoke filter rods.

10. A process as claimed in claim 9, wherein said an edible mineral oil.

2. A tobacco smoke filter as claimed in claim 1, wherein said lubricantfurther comprises 20 to 70 parts by weight of an edible mineral oil. 3.A tobacco smoke filter as claimed in claim 1, wherein the amount of saidlubricant in said fiber bundle is 0.5 to 5.0 percent based on the weightof said fiber bundle.
 4. A tobacco smoke filter as claimed in claim 2,wherein the amount of said lubricant in said fiber bundle is 0.5 to 5.0percent based on the weight of said fiber bundle.
 5. A tobacco smokefilter as claimed in claim 1, wherein said polyalkylene glycol etherresidue is selected from the group consisting of the ether residues ofpolyethylene glycol, polypropylene glycol, polyethylene-propylene glycoland poly-butylene glycol.
 6. A tobacco smoke filter as claimed in claim1, wherein said polyalkylene glycol ether residue consists of five to 30moles of glycol units.
 7. A tobacco smoke filter as claimed in claim 1,wherein said acyl group is selected from the group consisting of acidresidues of lauric acid, palmitic acid stearic acid, oleic acid, coconutfatty acid and beef tallow fatty acid.
 8. A tobacco smoke filter asclaimed in claim 1, wherein the fatty acid residue of said polyglycerinefatty acid ester is selected from the group consisting of acid residuesof lauric acid, palmitic acid, stearic acid, oleic acid, coconut fattyacid and beef tallow fatty acid.
 9. A process of manufacturing acellulose acetate fiber tobacco smoke filter which comprisesimpregnating a cellulose acetate filament tow with an aqueous emulsionof a lubricant containing 5 to 35 parts by weight of a polyalkyleneglycol fatty acid saccharose ether ester having the formula:
 10. Aprocess as claimed in claim 9, wherein said lubricant further comprises20 to 70 parts by weight of an edible mineral oil.